Dimethylformamide → N-[3-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-4-methoxy-benzenesulfonamide

HRID 655843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655843
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([NH2:17])=[C:11]3[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.CN(C=O)C>CO>[NH2:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:4]3[CH:3]=[C:2]([NH:1][S:26]([C:23]4[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=4)(=[O:28])=[O:27])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 119961041-(3-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Produkt 1

HCID 57750254N-[3-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-4-methoxy-benzenesulfonamideAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Title compound 11B, 1-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (36 mg, 1.1 eq, 0.16 mmol), 4-methoxybenzenesulphonylchloride (30 mg, 1.0 eq, 0.15 mmol) and diisopropylethylamine (25 μl, 1.0 eq, 0.15 mmol) were added to DMF (1 ml) and the mixture was stirred for 15 hours at room temperature under an inert atmosphere. Methanol was then added (1 ml) and the solvents were removed in vacuo. The resultant solid was purified by semi-preparative HPLC to yield the title compound as a white solid (30 mg, 0.08 mmol, 52%). LCMS: [M+H]+=397, Rt=1.68 min, 100% purity.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. customThe resultant solid was purified by semi-preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6962edaaced3438195932c1782fab6c4
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071607B2

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